Process for controlling the growth of unwanted plants

ABSTRACT

Process for controlling the growth of unwanted plants with NBeta -chloroethyl-N-lower alkyl or allyl-2,6-dinitro-4trifluoromethylanilines.

United States Patent Kiehs et al.

[451 Dec. 17, 1974 PROCESS FOR CONTROLLING THE GROWTH OF UNWANTED PLANTS Inventors: Karl Kiehs; Karl-Heinz Koenig,

both of Ludwigshafen; Adolf Fischer, Mutterstadt, allof Germany Assignee: Badische Anilin- & Soda-Fabrik Aktiengesellschaft, Ludwigshafen/Rhein, Germany Filed: May 11, 1973 Appl. No.: 359,242

Related U.S. Application Data Continuation-impart of Ser. No. 92,190, Nov. 23, 1970, abandoned, whioh is a division of Ser. No. 784,247, Dec. 16, 1968, Pat. No. 3,681,425.

Foreign Application Priority Data Dec. 21, 1967 ,Germany 1 43719 Primary Examiner-Lewis Gotts Assistant Examiner-Catherine L. Mills Attorney, Agent, or F [rm-Johnston, Keil, Thompson & Shurtleff [5 7] ABSTRACT Process for controlling the growth of unwanted plants with N-B-chloroethyl-N-lower alkyl or al1yl-2,6- dinitr0-4-trifluoromethylanilines.

2 Claims, N0 Drawings PROCESS FOR CONTROLLING THEGROWTH OF UNWANTED PLANTS RELATED APPLICATIONS This application is a continuation-in-part of our application Ser. No. 92,190, filed Nov. 23', 1970 now abandoned, which is a division of U.S. application Ser. No. 784,247, filed Dec. 16, 1968, now U.S. Pat. No. 3,681,425.

The present invention relates to a process for controlling the growth of unwanted plants with N-B-chloroethyl-N-lower alkyl or allyl-2,6-dinitro-4- trifluoromethylanilines.

An object of the invention is a process for controlling the growth of unwanted plants with minimum damage to crop plants. I

This and other objects of the invention are achieved by substituted dinitroanilines having the formula wherein R is allyl or lower alkyl (methyl, ethyl or propyl). These substituted dinitroanilines have good herbicidal action and, when compared with active ingredients of similar constitution, have superior plant compatibility.

The new compounds may be applied as herbicides. as solutions, emulsions, suspensionor dusts. The form of application depends entirely on the purpose for which the agents are being used; in any case it should ensure a fine distribution of the active ingredient.

For the preparation of solutions to be sprayed direct, mineral oil fractions with medium to high boiling points, such as kerosine or diesel oil coal tar oils and oils of vegetable or animal origin, cyclic hydrocarbons, such as tetrahydronaphthale'ne, and alkylated naphthalenes are suitable.

Aqueous formulations may be prepared from emulsion concentrates, pastes or wettable powders by adding water. To prepare emulsions the ingredients as such or dissolved in a solvent may be homogenized in water by means of wetting or dispersing agents, e.g., a polyethylene oxide adduct. Concentrates which are suitable for dilution with water may be prepared from active ingredient, emulsifying or dispersing agent and possibly solvent.

Dusts may be prepared by mixing or grinding the active ingredients with a solid carrier, e.g., diatomaceous earth or fertilizers.

The new compound may be prepared for example by reaction of substituted dinitrochlorobenzenes with substituted amines. They are crystalline or non-distillable oils;

The following Examples illustrate the preparation of specific compounds according to this invention.

EXAMPLE 1 Preparation of N-hydroxyethyl-N-allyl-2,6-dinitro-4- trifluoromethylaniline l0.l parts by weight of N-allyl-N-hydroxyethylamine is added to a solution of 13.5 parts by weight of 2,6- dinitro-4-trifluoromethylchlorobenzene in 50 parts by weight of dry tetrahydrofuran and the whole boiled under reflux for one to two hours. The solvent is then distilled off, the residue treated with ethyl acetate/waibility with Indian corn and soya beans.

ter, and the organic phase is removed and dried over sodium sulfate. After the ethyl acetate has been distilled off, the product is obtained as a red-brown oil (93 percent of the theory).

Analysis:

C H N calc.: 43.0 3.6 12.5 found: 43.2 3.6 12.0

EXAMPLE 2 Preparation of N -chloroethyl-N-allyl-2,6-dinitro-4- water and the organic phase is dried over sodium sulfate.

' After distilling off the solvent a dark brown oil (95 percent of the theory) is obtained from which, after purifying over silica gel'(benzene), yellow crystals may be isolated which have a melting point of 39 to 41C. Analysis:

C H N C1 calc.: 40.7 3.1 11.9 10.0 found: 40.4 3.2 11.6 9.9

Examples of substances prepared in the same way are the N-lower alkyl compoundsof the above formula wherein the alkyl group is methyl, ethyl or propyl instead of alkyl.

The following comparative experiment demonstrates the superiority of the compositions according to'this invention over known active ingredients.

EXAMPLE 3 In a greenhouse, loamy sandy soil is filled into pots and then sown with the seeds of cotton (Gossypium sp.), Indian corn (Zea mays), soya beans (Glycine hispida), annual meadow grass (Poa annua), orchard grass (Dactylis glomerata), slender foxtail (Alopecurus myosuroides) and barnyard grass (Panicul crus-galli).'

The soil prepared in this manner is treated with 3 kg hectare of N-allyl-N-B-chloroethyl-4- trifluoromethyl-2,6-dinitroaniline (l), and, for comparison, with 3 kg per hectare of N,N-dipropyl-4- trifluoromethyl-2,6-dinitroaniline (11), these amounts of the active ingredients each being dispersed in 500 liters of water per hectare. After four weeks it is ascertained that compound I, while having the same good herbicidal action as compound ll, has superior compat- The results of the experiment. may be seen from the following table:

0= no damage total destruction EXAMPLE 4 Loamy, sandy soil was sown with cotton (Gossypium hirsutum), rice (Oryza sativa), soya beans (Soja hispida), Indian corn (Zea mays), large crabgrass (Digitaria sanguinalis), giant foxtail (Setaria faberii), wild oats (Avena fatua), slender foxtail (Alopecurus myosuroides) and Italian ryegrass (Lolium multiflorum). The soil was then treated with I N-propyl-N-ethyl-2',6-dinitro-4- trifluoromethylaniline and, for comparison, with ll N-propyI-N-B-chloroethyl-2,6-clinitro-4- hectare of active ingredient and especially on Digitaria sanguinalis, Setaria faberii, Avena fatua and Lolium 'rnultiflorum, is considerably weaker than that of II.

TABLE I Active ingredient kglha 0.5 0.75 1.0 1.5 2.0 2.5 3.0

Crop plants:

Gossypium hirsutum 0 0 0 0 23 30 Oryza sativa 25 40 50 80 90 100 I00 Soja hispida 0 0 0 0 10 35 43 Zea mays 0 0 Unwanted plants:

Digitaria sanguinalis 90 90 95 I00 I00 100 Setaria faberii 5 7 90 95 I00 I00 I00 I00 Avena fatua 28 50 I00 I00 Alopecurus myosuroides S6 90 I00 I00 I00 I00 Lolium multiflorum 50 70 90 95 I00 I00 TABLE Continued.

Active ingredient kg/ha 0.5 075 L0 1.5 2.0 2.5 3.0

' Crop plants:

Gossypium hirsutum 0 0 0 0 0 4 l0 Oryza sativa 0 20 30 30 40 45 45 Soja hispida 0 0 0 0 l0 I0 I0 Zea mays 0 0 I5 25 30 35 40 Unwanted plants:

Digitaria sanguinalis 80 I00 I00 100 I00 I00 I00 Setaria faberii 7s 98 100 I00 100 I00 100 Avena fatua 50 80 95 I00 I00 I00 I00 Alopecurus myosuroides 70 I00 100 100 I00 I00 I00 Lolium multiflorum 75 95 I00 I00 I00 I00 100 0 no damage 5 l00=complete destruction We claim:

20 l. A process for controlling the growth of unwanted plants in cropswherein the soil in which the growth of the unwanted plants is to be prevented is treated with a phytotoxic quantity of a compound having the for- 35 where R denotes lower alkyl.

2. A process as claimed in claim 1 wherein 2,6- dinitro-4-trifluoromethyl-N-propyl-N-B- chloroethylaniline is used. 

1. A PROCESS FOR CONTROLLING THE GROWTH OF UNWANTED PLANTS IN CORPS WHEREIN THE SOIL IN WHICH THE GROWTH OF THE UNWANTED PLANTS IS TO BE PREVENTED IS TREATED WITH A PHYTOTOXIC QUANTITY OF A COMPOUND HAVING THE FORMULA
 2. A process as claimed in claim 1 wherein 2,6-dinitro-4-trifluoromethyl-N-propyl-N- Beta -chloroethylaniline is used. 